Propylamine → HCID 17838117, compound

HRID 1352142Notes

Reaction equation

HRID 1352142 reaction equation
[CH2:1]([NH2:4])[CH2:2][CH3:3].[NH:5]1[C:13]2[C:8](=[CH:9][C:10]([NH:14][CH:15]3[CH2:20][CH2:19][CH2:18][N:17]([CH:21]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[C:22](O)=[O:23])[CH2:16]3)=[CH:11][CH:12]=2)[CH:7]=[N:6]1.Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.CN(C1C=CC=CN=1)C.C(=O)([O-])O.[Na+]>CN(C)C=O>[CH2:1]([NH:4][C:22](=[O:23])[CH:21]([N:17]1[CH2:18][CH2:19][CH2:20][CH:15]([NH:14][C:10]2[CH:9]=[C:8]3[C:13](=[CH:12][CH:11]=2)[NH:5][N:6]=[CH:7]3)[CH2:16]1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:2][CH3:3]

Participants

8

Reactant 6

HCID 7852PropylamineHCID 218852-DimethylaminopyridineHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 17838237HCID 17838237, compound

Product 1

HCID 17838117HCID 17838117, compoundYield 73.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Propylamine (30 mg) and the compound prepared in Example 222 (88 mg) were dissolved in dimethylformamide (1 ml), and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (86 mg), 1-hydroxybenzotriazole (77 mg), and dimethylaminopyridine (5 mg) were added to the solution. The reaction mixture was stirred at room temperature for 18 hr. A saturated aqueous sodium hydrogencarbonate solution (1 ml) was then added thereto, and the mixture was extracted with chloroform-propanol (3/1). The organic layer was dried over anhydrous sodium sulfate, and the solvent was removed by distillation under the reduced pressure. The residue was purified by HPLC [chloroform/methanol] to give 72 mg of the title compound as two diastereomers (ratio=ca. 50:50).

Workup

  1. extractionthe mixture was extracted with chloroform-propanol (3/1)
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. customthe solvent was removed by distillation under the reduced pressure
  4. customThe residue was purified by HPLC [chloroform/methanol]

Sources & evidence

ORD record
ord-45912278df0c45aebc20d565ab14c5ba
Source dataset
uspto-grants-2007_05
Patent number
US07217722B2

Reaction notes

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